From a distance, it looked to the Tottenham Hotspur players like a mid-rise block of extremely exclusive apartments. Only when they got nearer did the full majesty dawn. It takes a particular level of wealth to draw the breath of a squad of Premier League footballers but it is safe to say that Joe Lewis and his super-yacht managed to do so.

It was the end of May and the manager, André Villas-Boas, and his players were in the Bahamas, ostensibly for an exhibition match against Jamaica but, really, for a bit of a wind-down. The season had just finished and, although it had brought a club record Premier League points tally, the achievement was undermined by the narrow failure to qualify for the Champions League.

The heartache was temporarily forgotten. Under the Caribbean sun, the players enjoyed the hospitality on Lewis's floating paradise; they took photographs like schoolboys. It was new territory on several levels. Lewis, the billionaire businessman who owns Tottenham, is a Keyser Söze figure. He is never heard and rarely seen. Lewis has entrusted the running of the club to the chairman, Daniel Levy.

But here he was, treating Villas-Boas and the players to a holiday. He was visible, at last. More than anything, though, it was a statement and nobody could ignore it. The guy-behind-the-guy is a serious player. Whatever he wants, he can make happen such as, for example, big contracts. His credit is good. Seeing and meeting Lewis was impressive and reassuring.

Tottenham have made a series of statements over the past 12 months or so. The club's new training ground has become a reality – it is state-of-the-art and magnificent – and the new stadium is in the pipeline. There was also Emmanuel Adebayor's permanent signing last summer. The striker earned £170,000 a week at Manchester City but Tottenham found a way to accommodate him. The wage ceiling has been raised and that makes players think. Perhaps, they can aspire to a top-level contract at White Hart Lane. Tottenham could be their destination club, as opposed to a stepping stone.

The encouragement has continued this summer. Villas-Boas, whose debut season was so nearly perfect and ended up as simply very good, turned down the chance to leave for Paris Saint-Germain. He has been conscious of the need to enter a second season at the same club for the first time in his short managerial career but the decision also reflected the faith that he has in the Tottenham project.

But Levy has stood his ground. He wants more – £100m or the cash-plus-player equivalent – and, right now, he is in a position to become the man that said no to world record money, who did not yield to the nine-times European champions.

Levy believes that with Bale and, possibly, a couple more decent buys, he could have a team to challenge for the title. He does not want to sell unless the proceeds can be translated into something that makes Tottenham collectively stronger before the closure of the transfer window. Not unusually, Levy feels that he can ask for the earth, despite having been offered several continents. He has pushed for the inclusion of the striker Alvaro Morata in the deal but Real do not want to lose their best young player.

Levy has form for grand resistance, most notably when he refused to sell Luka Modric to Chelsea in the summer of 2011; the west London club had offered a package worth £40m. Levy will surely remember how Modric was brilliant for Tottenham the following season, at least until March, when the whole team faded. He eventually sold him to Real last August for £33m. Levy also blocked the move that Dimitar Berbatov wanted to Manchester United in the summer of 2007 before he sanctioned it 12 months later for £30.75m.

It has been a tough time for Bale, who wonders whether the glamour move will materialise but Levy cares not for the 24-year-old's sensibilities. To him, Bale is a commodity and he would expect him to reapply himself after 2 September if he were to remain a Tottenham player. Given Bale's innate sense of duty, he probably would do.

It is fatuous to suggest that Bale has always wanted to wear the white of Real – he actually supported Arsenal as a boy – but, over the past few years, he has come to consider the Spanish club as the only one he wants to join. He has begun to learn Spanish and he is determined to seize the opportunity now. It is understandable that he may worry whether it would present itself again.

Bale has barely trained or played for Tottenham in pre-season, as he has carried minor injuries, albeit not ones that would threaten the completion of a Real medical and he does not want to risk exposing himself to any problem that could derail the move. It would be a surprise if Bale featured at all for Tottenham before the transfer deadline.

He finds himself stuck, unable to play or even to speak in public. It is an unedifying part of such situations that the player tends to feel the need to keep schtum, so as not to alienate the fans and sour his time at the club. Anybody, though, that still doubts Bale's desire to leave should consider this: if the daily reports about what he wanted to do were untrue, then either he or, more likely, Tottenham would have moved to set the record straight. Like many Premier League clubs, Tottenham are rarely slow to deny anything that they claim is wrong. They have said nothing.

It has to be added that Levy usually drives his negotiating opponent from the table at some point, in a state of anger, exasperation and/or bewilderment. "To Levy, every pound's a prisoner," said Jamie Redknapp, the former Tottenham midfielder. This is, therefore, one hell of a hostage situation.

Villas-Boas has insisted that the affair has not distracted his players but he was tense as he predicted a frenetic round of trading in the final week of the window and the associated struggle to start the season with a settled team. There was a marked transition to his squad last summer, with a lot of the signings coming late and it was perhaps no coincidence that the club stuttered at the outset, losing once and drawing twice in the league. How they would come to rue the dropped points in the final analysis.

"This last week in the transfer window can be surprising," Villas-Boas said after the 1-1 home draw against Espanyol. "We still have lots of things to do. There will be more players to arrive; there will be more players that are going to leave so, at this time, we are still a team in prospect."

Caulker, desperate for regular football, had feared that he would struggle behind Younès Kaboul, Jan Vertonghen and Michael Dawson in the White Hart Lane pecking order. Zeki Fryers, who arrived in January from Standard Liège, has stepped up from the development squad to feature at centre-half during pre-season.

Villas-Boas would like an upgrade at left-back, where Benoît Assou-Ekotto has been overlooked in pre-season – Danny Rose is in possession of the shirt – and there has been the usual transfer talk over Jermain Defoe, despite his love of all things Tottenham and preference to stay. With Soldado set to lead the line, Defoe and Adebayor may wonder whether they will enjoy sufficient minutes. Adebayor, though, is battling to come to terms with the death of his brother. His professional life has been placed into context.

Villas-Boas has reasons for optimism. He has arguably the league's best goalkeeper in Hugo Lloris; Kaboul and the midfielder Sandro are feeling their way back to fitness after long-term injuries; the signings thus far have been exciting and the likes of Moussa Dembélé, Gylfi Sigurdsson and Lewis Holtby will surely improve in their second seasons at the club. Holtby must first overcome a knee problem that has ruined his pre-season.

The coming two and a half weeks are likely to be intense. Tottenham will chase the stars, with exotic names like Willian of Anzhi Makhachkala, Roma's Erik Lamela and the 17-year-old Dynamo Zagreb midfield prodigy Alen Halilovic on the agenda. At the top of it, however, will be Bale.

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